In my more than 20 trips to countries around the world with the late Pope Francis, I never really knew what to say to him when he walked through the coach section of the papal plane, visiting the Vaticanisti like a flight attendant handing out peanuts. But when he made it to my middle seat as we headed to Cyprus this time, in December 2021, I had a plan. It was the fourth day of Hanukkah. And I was going to give the pope a dreidel.

Since Pope Paul VI in the 1960s, travel had become an important way to spread the papal message. John Paul II visited 129 countries. And like him, Francis was energized by the crowds and considered the visits the heart of his papacy. For the reporters on the papal beat, it was also essential, a way to observe him, understand him, engage him. And inundate him with gifts.

Over the years, he had been presented with a shoeshine kit and a shoeshine, a sombrero with his coat of arms, bags of Colombian coffee, watches, and a hand-painted ashtray, not to mention drawings or video messages made by the children of the Vaticanisti. Any letter Francis got was handed back in a no-look pass to his butler, who moved it along an assembly line of Vatican gendarmes until it ended in a bag, like the haul from a baby shower.

“On my desk,” Francis would say when he was given a letter he wanted to read and that should not be thrown in with the rest of the tchotchkes.

Some reporters greased their interview requests with homemade cakes or boxes of Argentinian alfajores cookies. Others ingratiated themselves with gifts in keeping with the pope’s priorities. A reporter from a Spanish Catholic publication, the undisputed queen of papal presents, gave the pope a painting of drowning Africans by a migrant who had survived a shipwreck, a shrapnel-pierced canteen that had saved the life of a Ukrainian soldier, gloves that environmental workers had used to clean a beach, and a copy of an ISIS tax imposed on Christians.

I had generally frowned on gift giving. It seemed overly deferential or transparently transactional and an echo of the magi bringing gifts to the manger or of courtiers bringing tribute to a Borgia. But after the tough COVID years, and with my deepening sense of the Italian perspective, I thought maybe it was rude to show up empty-handed.

So as he approached my seat, I reached into a crumpled paper bag and took out the only dreidel I could find in Rome, made of metal and expensive. I explained to Francis that the trip coincided with the Festival of Lights, when children played with the four-sided spinning top inscribed with Hebrew letters, and suggested he could kill some time on the flight playing with it up in first class with the cardinals.

The pope looked at me like I had a screw loose but graciously accepted the gift, though he mistook it for a bell and tried to ring it. I told him the winner of the dreidel game got Hanukkah gelt and handed him some gold-foiled chocolates. “These, I’ll pocket,” Francis said with a sly smile, pretending to slip the gelt in his cassock, which I didn’t think actually had any pockets.

“Happy Hanukkah!” I told him.

I grew up in Queens with Santa and dreidels, having been raised Jewish but with festive vestiges of my lapsed Irish Catholic mother’s upbringing. I never, to put it mildly, foresaw these two worlds colliding like this. After racing around Rome as a cub reporter for American newspapers, I returned to New York to chase the city’s power brokers for the Observer and later presidential candidates for the Washington Post and New York Times. Shortly after a pivotal 2016 election, I got the opportunity to return to Rome, family in tow, as the Times’ bureau chief. And while my colleagues in the States were transfixed by my old neighbor from Queens, my focus was firmly on Francis, trailing him anywhere and everywhere.

For the pope and the Vaticanisti who followed him, these trips were a break from the business of governing the church or covering it. For Francis himself, it was also an escape from his odd couple situation of sharing the Vatican gardens with his lingering predecessor, Benedict. Francis’s confidants told me that he sometimes complained about being cooped up in the Vatican, surrounded by enemies, especially during COVID.

By that point, I had spent years charting the ideological wars driven by conservative fears that Francis would torch church doctrine or lead some worldwide resistance to rising nationalists and populists. Vatican auditors had walked me through Francis’s financial reforms, and I made a point of meeting the new cardinals he installed, many from the Southern Hemisphere, where the church thrived as he sought to reorient it toward a more global future.

I tracked his efforts to make the church more welcoming and collegial, monitoring numbingly boring meetings with bishops as well as laypeople and eventually women, whose participation amounted to a revolution in church decision-making. And I felt the thrill of being present for something historic when he opened debate on issues such as divorce, same-sex couples, and an increased role for women.

I had also gotten used to Francis backtracking — the pope of radical change turned out to punt a lot. I once watched with other astonished reporters as he balked on approving the ordination of married men in remote parts of South America that had little access to the sacraments, a pragmatic reform that he had once signaled he wanted, but which was strongly resisted by Benedict and other conservatives.

But Francis was a pope of great, often outsize,........

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